8 Best High-Waisted Pants That'll Make Any Guy Look Better

Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.

This is every well-dressed guy's secret.

It seems like the menswear world is coming back around on a high-waist. Styleforum guys have always tried to look like Humphrey Bogart in pants up to their nipples, and the average man has been sold mid-rise, tight performance chinos. The ideal is somewhere in the middle, though admittedly, it's closer to what the menswear nerds want you to wear.

High-waisted pants are beloved here at Esquire. We just published an ode to the old-school chino, plus praise for the J.Crew Giant Fit and its competitors. We've endorsed a Buck Mason Full Saddle Jean and the Wrangler Cowboy Cut, both high waisted and universally flattering. Because that's the thing, when pants sit at your natural waist, or above it if you have a long torso, they make you look taller, slimmer, and (probably) more handsome.

Don't get me wrong, I love a Lenny Kravitz low-rise flared jean, but you've got to keep the body tight for that to work. When a regular guy, or even a celebrity, wants to look a little better, they reach for something that sits up near their belly button. It's just the laws of nature, the Golden Ratio, proportions. If you're on a quest for the perfect pants, here are our eight favorite high-waisted pants of the moment.

Most guys that get into menswear these days start with a Dickies 874. When you're in high school or college looking for pants that look nice but can be purchased on a waiter's salary, Dickies is always there.

Like most work pants, the 874 has a high rise for functional purposes. It gives you room to bend down, move around, and work. But if you keep a black, navy, or brown pair of Dickies pristine and creased, they can cosplay as a pair of more expensive pair of pants.

All that makes them the ideal pants to try out a high waist in. Get a pair, put them on, and look in the mirror. For a few weeks, replace your jeans with a pair of Dickies. If you like what they do for you, move on to the rest of the list.

My oldest brother, a skate kid in the early 2000s, got me into Ben's. They're cut a little higher than Dickies, and the twill is a bit thicker. Fair warning that the original cut is healthy; Gorilla cut is huge. I wear the trim fit, and they fit me like high fashion pants: slim through the seat and thigh, straight stovepipe fit from the knee down.

The easiest way to find a high-rise pant is to go Gurkha. The style is pulled from old British military travels to northern India and Nepal. It features an extended adjustable waistband. The Todd Snyder version isn't the highest-rise Gurkha you can find, but it's more than enough to qualify.

These pants sit at your natural waist, but four pleats give you room to breath around the seat and thighs. Then, they taper down to the hem to give a more professional, less military, look.

Buck Mason does a great job of adapting old military and workwear inspiration for the average guy. These chinos are the perfect example.

I've already pledged my Wrangler allegiance on this website. For the money, there's not a better pant than the rigid indigo raw denim Cowboy Cuts. Just beware, this original cut is still pretty slim. Go for the relaxed cut if that's a worry. Little guys and rockstars can do the slim cut.

And if you're worried about looking too cowboy, just cut the back patch off when you get them. Problem solved.

This is what we'd put most guys off the street in. Drake's, our favorite ready-made British suit maker, has a flat front chino. It's high rise, relaxed through the seat, with a taper. These pants look fantastic with a sneaker, even better with a hard-bottom shoe.

This hasn't been widely advertised stateside, but Edward Sexton does ready-to-wear. This is a dream for me, who inherited a Beatles and Rolling Stones obsession and always had the late eponymous tailor as a fashion North Star. Now regular guys, like you and I, can get that Nutters look for a reasonable price.

Everything in the collection is high rise, so pick what you're into. The classic cut is an adaptation of the original Nutters look to today's tastes. But if you want to go for it, you can. The Hollywood Trousers feature an ultra-high-rise Hollywood waist, too much of a menswear nerd affectation if you ask me, but live your truth. The Parallel Trouser is classic '60s Sexton. The flares are incredible, and the Oxford Bags are Sexton take on a classic chino. It's all second-to-none.

I've got love for Factor's because it's a freaky little bespoke tailor out of my home state, but the clothes can speak for themselves. Core to the ready-to-wear section are Factor's trousers. These pair workwear influences, like the easy-entry Ben Davis pocket, with a tailor's obsession with fabric. Other fabrics come and go from the lineup, but this Midnight Mohair is a staple. It's a fabric developed just for Factor's: 70/30 wool/mohair with black yarns interwoven with the navy. The result is that nighttime sky blue, a crisp feel, and this wonderful tux-like sheen from the mohair.

As for the fit, off the rack they're pretty generous all the way down from your natural waist. Factor's cuts everything unisex, so they'll fit great if you've got hips, or drape off you if you don't. A fucking great pair of pants.

We’re not going to say something is great unless it’s actually great.

Every product in Esquire’s round-ups is carefully curated by our fashion and e-commerce teams. When it comes to high-waisted pants, you can rest assured that we’re hand-selecting styles that we’ve personally tested, tried, and loved, along with styles that the rest of our fashionable colleagues here at Esquire endorse for their own wear.

We’ve had to go through a lot of trial and error, and these high-waisted pants are the ones that are simply the best. Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for advice from folks who care (possibly too much!) about this sort of stuff, this is the place to start.

The 11 Best Field Watches You Can Buy Right Now

The 8 Best Linen Sofas of 2025

Best Early Prime Day Tech Deals of 2025

Prime Day 2025 Oura Ring Sales

The Best Shoes for Standing All Day

Save 50% on Top Brands at the REI Summer Sale

Shop Early Prime Day Mattress Deals for Better Zzs

The 7 Best Rain Jackets for Men in 2025

9 Best Heavyweight T-Shirts of 2025

The 13 Best Harrington Jackets for Men of 2025

The Best Apple Deals Ahead of Amazon Prime Day

Shop Amazon’s Best Menswear Deals for Prime Day